The present invention relates to 1-oxyalkyl-2,6,6-trimethylcyclohexene derivatives defined by the generic structure: ##STR8## wherein R.sub.1 is one of OH, ##STR9## OMgX or H; R.sub.2 is ##STR10## OH, OMgX, CH.sub.3, H; R.sub.3 is one of methyl, ethyl, 1-propyl or 2-propyl; X is chloro, bromo or iodo; R.sub.6 is hydrogen or no moiety; one of the wavy lines is a carbon-carbon double and the other of the wavy lines is a carbon-carbon single bond; with the first proviso that when the .DELTA..sup.2,3 bond is a carbon-carbon double bond, then R.sub.6 is hydrogen and the moieties R.sub.6 and ##STR11## are so juxtaposed as to give rise to two different groups of stereoisomers of the molecular genus: ##STR12## and with the second proviso that when R.sub.1 is one of ##STR13## OH or OMgX then R.sub.2 is hydrogen or methyl; and when R.sub.2 is one of ##STR14## OH or OMgX then R.sub.1 is hydrogen.
These compounds are prepared by straightforward economical process also covered by this invention. Said process is illustrated by the following reaction sequence: ##STR15## wherein R.sub.4 and R.sub.5 are each the same or different and each represents hydrogen, methyl or ethyl and the sum, "s" of carbon atoms in R.sub.4 and R.sub.5 taken together is governed by the mathematical inequality 1.ltoreq.S.ltoreq.2.
The present invention also provides for the utilization of several compounds produced by our invention and several mixtures produced by the process of our invention for augmenting or enhancing the aroma or taste of foodstuffs, foodstuff flavoring compositions, chewing gums and medicinal products.
There is a continuing search for foodflavor compositions which can vary, fortify, modify, enhance, augment or otherwise improve the flavor and/or aroma of foodstuffs, medicinal products, toothpastes and chewing gum. To be satisfactory, such compositions should be stable, non-toxic and blendable with other ingredients to provide their own unique flavor and aroma nuances without detracting from the contributions of the co-ingredients. Preferably, such compositions should be naturally occurring or present in natural foodstuffs so that their ingestible safety can be readily recognized. These materials should be capable of being synthesized in a simple and economical manner. The need for safe flavors in the berry fruit flavor area, especially the raspberry area, the blueberry flavor area and the apple flavor area is well known particularly in the fruit juice, ice cream and yogurt flavor areas. In addition, there is a need for the development of non-toxic materials which can replace natural materials not readily available having camphoraceous, herbaceous, minty, musty/earthy, oriental, floral/oriental, fruity, raspberry-like, sweet, peach-like, woody, damascenone-like and tobacco like aroma and flavor characteristics.
Such aroma and taste nuances are particularly useful in the raspberry flavor, peach flavor, dried fruit flavor, apple flavor, blueberry flavor, nut flavor, peppermint flavor and tobacco like flavor containing foodstuffs.
The instant invention provides the foregoing which the prior art has heretofore failed to provide. Furthermore, nothing in the prior art shows the unexpected, unobvious and advantageous value of carrying out reaction of an alkyl Grignard reagent with betacyclocitral, alphacyclocitral, betahomocyclocitral or alphahomocyclocitral which compounds are themselves known for their organoleptic uses and which are readily and economically available.
Swiss Pat. No. 557,422 discloses for use in perfumery compounds having the structures: ##STR16## Nothing in the prior art however, discloses the flavor use of the compounds disclosed in the instant specification and furthermore, nothing in the prior art discloses the organometalic compounds of our invention having the generic structure: ##STR17## wherein one of the wavy lines is a carbon-carbon double bond and the other of the wavy lines is a carbon-carbon single bond; wherein n is zero or 1; wherein X is chloro, bromo or iodo; and wherein R.sub.4 and R.sub.5 are each the same or different and each represents hydrogen, methyl or ethyl; and wherein the sum, "s," of carbon atoms in R.sub.4 and R.sub.5 taken together as governed by the mathematical inequality 1.ltoreq.S.ltoreq.2.